Chemospecific Cyclizations of α‐Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls



Clare, Daniel, Dobson, Benjamin C, Inglesby, Phillip A and Aïssa, Christophe ORCID: 0000-0003-0750-9435
(2019) Chemospecific Cyclizations of α‐Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls. Angewandte Chemie, 131 (45). pp. 16344-16348.

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Abstract

<jats:title>Abstract</jats:title><jats:p>The functionalization of aryl and heteroaryls using α‐carbonyl sulfoxonium ylides without the help of a directing group has remained so far a neglected area, despite the advantageous safety profile of sulfoxonium ylides. Described herein are the cyclizations of α‐carbonyl sulfoxonium ylides onto benzenes, benzofurans and <jats:italic>N</jats:italic>‐<jats:italic>p</jats:italic>‐toluenesulfonyl indoles in the presence of a base in HFIP, whereas pyrroles and <jats:italic>N</jats:italic>‐methyl indoles undergo cyclization in the presence of an iridium catalyst. Significantly, these two sets of conditions are chemospecific for each groups of substrates.</jats:p>

Item Type: Article
Uncontrolled Keywords: 3405 Organic Chemistry, 34 Chemical Sciences
Depositing User: Symplectic Admin
Date Deposited: 19 Nov 2019 17:06
Last Modified: 20 Jun 2024 17:10
DOI: 10.1002/ange.201910821
Related URLs:
URI: https://livrepository.liverpool.ac.uk/id/eprint/3062445